This invention relates to 1-benzopyransulfonamides, 1-benzothiopyransulfonamides, 1-benzoxepinsulfonamides and 1-benzothiepinsulfonamides which are useful as plant growth regulants and in particular as herbicides.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, discloses the preparation of compounds of the following Formula and their use as general or selective herbicides: ##STR1## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 R.sub.2 is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl. PA1 R.sub.4 is hydrogen, fluorine, chlorine, bromine or methyl; PA1 R.sub.5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy; PA1 R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atom; PA1 R.sub.8 is hydrogen, methyl, chlorine or bromine; PA1 R.sub.9 and R.sub.10 are independently hydrogen, methyl, chlorine or bromine; PA1 W and Q are independently oxygen or sulfur; PA1 n is 0, 1 or 2; PA1 X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S-- or CH.sub.3 OCH.sub.2 --; and PA1 Z is methyl or methoxy; PA1 (a) when R.sub.5 is other than hydrogen, at least one of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 is other than hydrogen and at least two of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be hydrogen; PA1 (b) when R.sub.5 is hydrogen and all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 are other than hydrogen, then all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be either chlorine or methyl; and PA1 (c) when R.sub.3 and R.sub.7 are both hydrogen, at least one of R.sub.4, R.sub.5 or R.sub.6 must be hydrogen. PA1 R.sub.1 is H, CH.sub.3, OCH.sub.3, Cl, Br, CO.sub.2 R.sub.5, SO.sub.2 R.sub.6, OSO.sub.2 R.sub.7 or SO.sub.2 NR.sub.8 R.sub.9 ; PA1 R.sub.4 is H or CH.sub.3 ; PA1 R.sub.2 and R.sub.3 are independently H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.5 is C.sub.1 -C.sub.3 alkyl, CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 CH.sub.2 OCH.sub.3 or CH.sub.2 CH.sub.2 Cl; PA1 R.sub.6 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.7 is C.sub.1 -C.sub.3 alkyl or CF.sub.3 ; PA1 R.sub.8 and R.sub.9 are independently C.sub.1 -C.sub.2 alkyl; PA1 A is ##STR9## X is CH.sub.3, OCH.sub.3 or Cl; Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, NH.sub.2, NHCH.sub.3 or N(CH.sub.3).sub.2 ; PA1 Z is CH or N; PA1 G is O or CH.sub.2 ; and PA1 X.sub.1 is CH.sub.3, OCH.sub.3 or OC.sub.2 H.sub.5 ; PA1 (1) when X is Cl, then Z is CH and Y is OCH.sub.3, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2 or OC.sub.2 H.sub.5 ; PA1 (2) the total number of carbon atoms in R.sub.2 and R.sub.3 are less than or equal to 3; PA1 (3) in Formula J.sub.2, when R.sub.2 and R.sub.3 are other than H, then R.sub.4 is H; PA1 (4) in Formula J.sub.3, when R.sub.2 is other than H, then R.sub.4 is H; PA1 (5) when Q is S, then R.sub.1 is not SO.sub.2 NR.sub.8 R.sub.9 ; PA1 (6) in Formulae J.sub.3 and J.sub.6, Q may not be O; PA1 (7) in Formula J.sub.7, R.sub.1 is not CH.sub.3. PA1 (1) Compounds of Formula I where J is J.sub.1. PA1 (2) Compounds of preferred 1 where R is H. PA1 (3) Compounds of preferred 2 where R.sub.1 is H. PA1 (4) Compounds of preferred 3 where A is ##STR10## and X is OCH.sub.3 or Cl. (5) Compounds of preferred 4 where Y is CH.sub.3 or OCH.sub.3. PA1 (6) Compounds of Formula I where J is J.sub.2. PA1 (7) Compounds of preferred 6 where R is H. PA1 (8) Compounds of preferred 7 where R.sub.1 is H. PA1 (9) Compounds of preferred 8 where A is ##STR11## and X is OCH.sub.3 or Cl. (10) Compounds of preferred 9 where Y is CH.sub.3 or OCH.sub.3. PA1 (11) Compounds of Formula I where J is J.sub.3. PA1 (12) Compounds of preferred 11 where R is H. PA1 (13) Compounds of preferred 12 where R.sub.1 is H. PA1 (14) Compounds of preferred 13 where A is ##STR12## and X is OCH.sub.3 or Cl. (15) Compounds of preferred 14 where Y is CH.sub.3 or OCH.sub.3. PA1 (16) Compounds of Formula I where J is J.sub.4. PA1 (17) Compounds of preferred 16 where R is H. PA1 (18) Compounds of preferred 17 where R.sub.1 is H. PA1 (19) Compounds of preferred 18 where A is ##STR13## and X is OCH.sub.3 or Cl. (20) Compounds of preferred 19 where Y is CH.sub.3 or OCH.sub.3. PA1 (21) Compounds of Formula I where J is J.sub.5. PA1 (22) Compounds of preferred 21 where R is H. PA1 (23) Compounds of preferred 22 where R.sub.1 is H. PA1 (24) Compounds of preferred 23 where A is ##STR14## and X is OCH.sub.3 or Cl. (25) Compounds of preferred 24 where Y is CH.sub.3 or OCH.sub.3. PA1 (26) Compounds of Formula I where J is J.sub.6. PA1 (27) Compounds of preferred 26 where R is H. PA1 (28) Compounds of preferred 27 where R.sub.1 is H. PA1 (29) Compounds of preferred 28 where A is ##STR15## and X is OCH.sub.3 or Cl. (30) Compounds of preferred 29 where Y is CH.sub.3 or OCH.sub.3. PA1 (31) Compounds of Formula I where J is J.sub.7. PA1 (32) Compounds of preferred 31 where R is H. PA1 (33) Compounds of preferred 32 where R.sub.1 is H. PA1 (34) Compounds of preferred 33 where A is ##STR16## and X is OCH.sub.3 or Cl. (35) Compounds of preferred 34 where Y is CH.sub.3 or OCH.sub.3. PA1 N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-3,4-dihydro-2H-1-benzot hiopyran-8-sulfonamide, 1,1-dioxide; PA1 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3,4-dihydro-2H-1-benzothiopy ran-8-sulfonamide, 1,1-dioxide; and PA1 N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-3,4-dihydro-2H-1-b enzothiapyran-8-sulfonamide, 1,1-dioxide.
U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR2## wherein: R.sub.1 is hydrogen or lower saturated aliphatic acyl and
The disclosed compounds are said to provide control of crabgrass, cress, endive, clover and Poa annua.
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides as being useful as antidiabetic agents: ##STR3## wherein R=H, halogen, CF.sub.3 or alkyl.
Logemann et al., Chem. Ab., 53, 18052g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR4## wherein R is butyl, phenyl or ##STR5## and R.sub.1 is hydrogen or methyl.
When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR6##
U.S. Pat. No. 4,127,405 teaches compounds which are useful for controlling weeds in wheat having the formula ##STR7## R.sub.3 and R.sub.6 are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH.sub.3 S(O).sub.n -- or CH.sub.3 CH.sub.2 S(O).sub.n --;
or their agriculturally suitable salts; provided that:
In addition, U.S. Ser. No. 227,886 teaches o-alkylsulfonylbenzenesulfonylureas which are useful as herbicides.
In U.S. Ser. No. 274,233, there is a disclosure of herbicidal benzo[b]thiophene- and benzofuransulfonylureas in which the sulfonylureido group is bonded to the heterocyclic ring.
In U.S. Ser. No. 363,379, there is a disclosure of herbicidal benzodioxole- and benzodioxansulfonylureas, while in U.S. Ser. No. 312,183, herbicidal benzofuran- and benzothiophenesulfonylureas are disclosed in which thiosulfonylureido group is bonded to the benzo ring.
Undesired vegetation can cause substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, soybean and the like.
Although a wide variety of materials are available which can be used for killing or inhibiting (controlling) the growth of undesired vegetation the need exists for still more effective herbicides that destroy or control weeds without causing significant damage to useful crops.